Dimethylacetamide → HCID 90082820, compound

HRID 2276873Notes

Reaction equation

Br[C:2]1[CH:27]=[C:26]([O:28][CH3:29])[C:5]2[NH:6][C:7](=[O:25])[CH:8]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C[C:31]([N:33](C)C)=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:31]([C:2]1[CH:27]=[C:26]([O:28][CH3:29])[C:5]2[NH:6][C:7](=[O:25])[CH:8]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1)#[N:33]

Participants

Conditions

Temperature: 90 °C

Procedure

tert-Butyl (7-bromo-9-methoxy-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)carbamate (0.050 g, 0.109 mmol), zinc cyanide (0.013 g, 0.109 mmol), and Pd(Ph3P)4 (0.013 g, 10.86 μmol) were dissolved in DMA (0.543 ml) and heated to 90° C. After 1 h, the reaction was quenched with saturated NaHCO3. The reaction mixture was extracted three times with EtOAc. The combined organic layers were dried with MgSO4 and evaporated. The residue was purified by silica gel chromatography (hexanes/EtOAc) to give tert-butyl 7-cyano-9-methoxy-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamate (41 mg, 93%): HPLC RT=1.948 min (H2O/MeOH with TFA, SunFire C18, 5.0 μm, 2.1 mm×30 mm, 4 min gradient, monitored at 220 nm). [M+H+]=407.

Workup

customthe reaction was quenched with saturated NaHCO3
extractionThe reaction mixture was extracted three times with EtOAc
dry with materialThe combined organic layers were dried with MgSO4
customevaporated
customThe residue was purified by silica gel chromatography (hexanes/EtOAc)

Sources & evidence

ORD record: ord-02c2800a10f44d5a85632b142ca5a33e
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133139B2

Reaction notes

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